Enantioselective PCCP Brønsted acid-catalyzed aza-Piancatelli rearrangement

• Gabrielle R. Hammersley,
• Meghan F. Nichol,
• Helena C. Steffens,
• Jose M. Delgado,
• Gesine K. Veits and
• Javier Read de Alaniz

Beilstein J. Org. Chem. 2019, 15, 1569–1574, doi:10.3762/bjoc.15.160

• acid; cyclopentane; furylcarbinols; PCCP; Introduction The discovery of a wide range of cyclopentane containing natural products [1][2] and biologically active molecules such as palau’amine [3][4], agelastatin A [5][6][7], pactamycin [8][9][10], and aristeromycin [11][12], has created a demand for new

Formal synthesis of (−)-agelastatin A: an iron(II)-mediated cyclization strategy

• Daisuke Shigeoka,
• Takuma Kamon and
• Takehiko Yoshimitsu

Beilstein J. Org. Chem. 2013, 9, 860–865, doi:10.3762/bjoc.9.99

• intermediate for the synthesis of (−)-agelastatin A (AA, 1), a potent antiproliferative alkaloid. The present synthetic endeavour offered an insight into the mechanism underlying the iron(II)-mediated aminohalogenation of N-tosyloxycarbamate, in which the radical properties of the N–iron intermediates in the

• redox states were operative. Keywords: agelastatin; aminohalogenation; iron(II); free radical; natural product synthesis; Introduction Marine organisms often produce bioactive substances that potentially serve as attractive resources for drug discovery. (−)-Agelastatin A (AA, 1), a cytotoxic alkaloid

• have developed a new approach to key compounds 5a/5b for (−)-agelastatin A (1) synthesis, which features the iron(II)-mediated radical cyclization of N-tosyloxycarbamate, a safe azidoformate surrogate. Although somewhat moderate chemical yields of the compounds were obtained in this study, the